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Barry Diller: Hollywood Tycoon’s Life of Deceit and Dysfunction

At the age of 83, business tycoon Barry Diller has embarked on his book tour, although it seems he’s having second thoughts about the whole endeavor. ‘I’m shortening the tour part,’ Diller confessed in his distinctive voice, known to many as the ‘Killer Diller.’ The voice that, for many decades, both terrified and captivated Hollywood doesn’t seem to have the same power when it pertains to personal scrutiny. ‘I am not up for interrogation on aspects of my personal life,’ he pointedly stated as we settled into our conversation in the posh setting of his Art Nouveau quarters in the Carlyle hotel.

Comparing the initial introductory paragraph of his coming-of-age story, ‘Who Knew’, stands testament to his newly found reluctance. Diller begins the book with an unapologetically honest description of his formative years. Dysfunction glued the bond of the very household he grew with – a family representing a less-than-ideal portrait. His parents walked on thin ice towards divorces on multiple occasions, and his brother dabbled with drug addiction by the tender age of 13. Diller himself, cloaked in secrets and sexual confusion, started his journey into this tumultuous world at the age of 11.

With the release of his book, Barry Diller has confirmed a widely speculated but never publicly acknowledged truth about his personal life – he identifies as gay. To be more precise, Diller discloses his bisexuality. In his own words, ‘While there have been a good many men in my life from the age of 16, there has only ever been one woman.’ That one woman – the seductive Princess of Wrap, Diane von Furstenberg – entered his life during the extravagance of the Studio 54 era. She prided herself on being the first woman he was intimate with, leading to a passionate affair that eventually blossomed into a liberated and contentedly unorthodox marriage.

Close friends of von Furstenberg and Diller watch in awe as the latter opens up for the first time about his unique personal life. Known for his blunt demeanor and business pragmatism, Diller often finds himself referred to by Netflix CEO Ted Sarandos as ‘one of the very few who doesn’t care what people think in a town full of people who do care.’ Such aphorism, although fitting for Diller’s professional life, doesn’t quite hold up when considering his personal matters – more specifically, his sexuality.

Diller chose this moment to share his life’s journey and his stratospheric career. ‘I wanted to tell the story,’ he said, stressing on his commitment to revealing the truth, however uncomfortable it might appear. Although Diller had successfully managed to conceal his personal life behind a veil of discretion, he found it challenging to finally lift the shroud, making his private life public.

Diller crafted his ‘Bill of Rights’ early on, representing his unique approach towards handling his sexuality within the business community. He chose neither to declare his sexuality openly, nor camouflage it beneath a veil of heterosexuality by succumbing to societal expectations of masculinity. Retrospectively, he refers to that time as being ‘chicken,’ insinuating a struggle with self-acceptance.

He paints a vivid picture of the arduous path many walked during those times, living life in a state of self-imposed exile, stunted in their true expression. ‘Consider if you can what such a daily drip of that kind of dysfunctional life does to one’s sense of self,’ he writes in a reflective tone. These are the musings of a man who has lived through the many shades of life, albeit discreetly.